


Dressed Like a Man, Fucked a Woman

by Mistress_Cobra



Category: Tom Hiddleston - Fandom
Genre: Anal Sex, Being Gagged, Cunnilingus, Desk Sex, Dirty Talk, Do Not Go From Anal to Vaginal Sex Without Protection, Dubious Consent, Dubious Consent to Full Consent, F/M, Light Bondage, Light Dom/sub, NSFW, Oral Sex, Orgasm Control, Orgasm Denial, Rimming, Spanking, cross-dressing
Language: English
Status: Completed
Published: 2014-09-19
Updated: 2014-09-19
Packaged: 2018-04-27 15:50:20
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,885
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5054686
Author URL: https://archiveofourown.org/users/Mistress_Cobra/pseuds/Mistress_Cobra
Summary: <blockquote class="userstuff">
              <p>Nameless OFC is a young cross-dressing college student. She enjoys wearing men’s clothes and hiding her feminine side from others. Professor Hiddleston respects her individuality but is mildly distracted from time to time by her and can’t seem to contain himself much longer.</p>
            </blockquote>





	Dressed Like a Man, Fucked a Woman

Professor Hiddleston is quite possibly the coolest professor I’ve ever known. He teaches English Literature and one can tell this is his passion, but he’s also stern & doesn’t take shit from students. Some may say he’s a no-nonsense kind of man and not sociable, but I’ve always felt comfortable around him & could talk to him about any and every thing. He’s never judged me once from day one since I first entered his classroom when the semester started.

I am a cross-dressing woman. I enjoy and prefer wearing men’s clothes and I’ve dressed this way since my early teen years. I’m very much straight, I even had a boyfriend for 4 years, but it astounds me how quickly so many assume otherwise. Some even said my relationship ended because they thought I came out, but really, it was just compatibility issues, nothing more. It still amazes me how so many are uncomfortable around me over something so silly as the way I dress. The only thing that made my womanhood obvious were my voluptuous hips and ass since my bosom wasn’t really that well endowed, so wearing a bra seemed pointless to me. However, even in my baggiest camouflage pants, my buttocks stood out rather obviously.

Professor Hiddleston, however, greeted me with a smile and a nod every day just like he would anyone else when I started taking his class. I would even sit and chat with him about his lessons and our different hobbies. It appears we’re both shut-in types that prefer solitude over social scenes. I’m pretty sure he’s got a girlfriend, even though he’s never mentioned one. I assume he had one because it seemed like every other day, a young pretty college girl would approach him, brazenly asking him out for coffee, drinks at a bar, or something but he would just politely turn them away, telling them it’s not professional for a professor to court students, and ask them to turn their interests towards the male-student body.

One lazy Saturday afternoon, he was finished for the day and dismissed his class and while the rest of the students left, like usual, I stayed behind to discuss his latest teachings, among other things. He seemed distracted or agitated today, and I admit, I was mildly concerned. My ensemble today was a black button-up shirt with long sleeves rolled up to my elbows, a crimson red tie, and black dress pants with simple black flip-flops.  
“Professor Hiddleston, may I be a bit bold with you?” I asked curiously but cautiously.  
His blue eyes shocked me when he turned to look at me. His lips were pressed in a tight thin line amongst his scruffy beard. He sighed with exasperation, running his right hand through his wavy ginger hair.

“Always, dear. And would you be so kind to shut my door for me, please?” He queried with a hushed but desperate tone. I shrugged, walked over towards the entrance & closed his classroom door, and just because he seemed like he needed some alone time, I locked it for him as well. Maybe I made him upset? Was he mad about something? Is something troubling him, perhaps? It was unlike him to act so strangely all of the sudden. As I approached him, he leaned against his desk, his arms were crossed, his gaze was downcast. He seemed conflicted about something as I heard his voice hum in his throat.

“I need to ask you a question, dear.” Professor Hiddleston’s voice was low as he glared up at me. Shit, was he angry at me?

“Uuh… Yeah, shoot. What is it?” My voice was a bit broken, his demeanor was a bit unsettling. His gaze was smoldering and he licked his lips as he stared directly at my chest, and I could feel my nipples starting to harden noticeably through my shirt. I felt my cheeks suddenly burning and I felt my heart racing as his eyes lingered for a moment and then directly into my wide and very much flustered stare.

“Why are you not wearing a bra, love?” His English voice was husky and my jaw dropped at his bold question.

“Professor Hiddleston, why the hell would you ask me that?!” I kept my voice down but I couldn’t contain my embarrassed and admittedly somewhat angry state.  
I was unprepared for his lightning fast reaction as he grabbed my tie and pulled my body close, wrapping his other arm around me and his lips captured my agape mouth. I whimpered as his tongue dominated mine and explored my mouth in the fiery kiss. He began to pull away slightly but caught my tongue in his teeth, suckling it, and groaned as his hips bucked against me. When he released me, I gasped for air, panting breathlessly as my senses were overwhelmed by his kiss, the taste of earl grey tea from his mouth, the smell of his cologne, and his smoldering eyes. Oh God, I wanted him but I was so confused. I thought he didn’t care for college girls like me. I also didn’t think he’d find me desirable in this sense.

“Do you know how distracting you are in my class, young lady?” He smirked as his hands squeezed my breasts and I couldn’t help but moan and whimper as he kneaded and massaged my small mounds.

“Wh-what are you t-t-talking about?” I breathed huskily but my question made him chuckle. He dipped his head down and his hot breath teased what little flesh of my exposed neck shown.

“My dear, I admire your individuality as a woman who chooses to dress with masculinity. However, you have no idea how much of a tease you are being whenever my classroom gets chilliest in the slightest, and I can see your nipples begging for attention.” He whispered with a growl, biting my earlobe and I quivered.

“I didn’t think… they were noticeable.” I whispered, I could feel my ears now turning rosy like my cheeks. “Professor Hiddleston…” I started.

“Thomas, darling.” His silken voice corrected.

“Thomas, I didn’t think you…were interested in college girls my age.” I whispered but his response was another soft chuckle as he undid my tie, placing it on his desk, repeating the process with his own blue tie. He took my chin in his long fingers, tilting my head up to meet his baby blue eyes, gazing deeply into mine while licking his lips.

“Normally, I’m not however… Your beauty is different, you captivate me and sometimes at night, I have found myself imagining what you really look like underneath those clothes, stroking myself to the thought of kissing you, tasting you, and fucking you.” He groaned, grinding his hips into me and there was no mistaking the hard-on that was demanding attention underneath his pants’ material. I was so flustered, flattered, and aroused, but still mildly unsure of this situation.

“Thomas, I don’t want you to jeopardize your job over this.” I whispered but was silenced when his fingertip touched my lips, his smoldering gaze almost made me forget to breathe. I gasped when he hoisted me up and sat me on top of his desk.

“Just hush, darling.” His voice purred as his nimble fingers made quick work of the buttons of my shirt, and his large hands slid over my shoulders and arms delicately as he took my shirt off, exposing my bare chest. I shuddered as his hands cupped my small breasts, brushing the pads of his thumbs over my tiny pink nubs. “So adorable…” Thomas cooed before leaning down and flicked his tongue over my right nipple, eliciting a gasp from my mouth.

“Ahh, Th-Thomas…!” I whined, fidgeting under his every touch. I bit back a moan as his mouth encompassed my right breast, suckling the nub while his hand pinched and teased the left. His tongue flicked, swirled, and lapped at my nipple while his scruffy beard would scratch and tickle the flesh around my breast, forcing me to tilt my head back and moan softly. After a brief moment, he swapped places and began to nip and suckle at my left nipple while his hand unbuttoned and unzipped my pants. He looked down to see that I was wearing a crimson red silk thong with purple embroidered designs.

“Oh la, la, darling… You dress like a man outwardly, but your taste in lingerie is interesting.” Thomas grinned and I smiled bashfully. I did have some feminine taste when it came to undergarments. He craned his head into the crook of my neck, his tongue skimmed along the flesh and then across my shoulder.  
“Let’s get you out of these, shall we?” His voice growled while he jerked my pants and thong down around my ankles and discarded them into the floor. I gasped when his nose brushed the sensitive flesh of my sex, inhaling my scent and groaned. He gently pushed me back to where I was laying completely flat on his desk now. I quivered as he spread my legs apart and gazed upon me.  
“Th-Thomas…” I whimpered, growing more flustered as his face lowered between my legs and I could feel his hot breath washing over the sensitive flesh. He looked up at me with a stern glare.  
“Me thinks the lady doth protest too much.” Thomas growled as he loomed over my body, reaching for something. I was surprised when he presented our ties and gently wrapped mine around my mouth and knotted it in the back, effectively silencing my words, while using his to tie my wrists together above my head. “Darling, I am going to taste you and then fuck you like the beautiful woman you truly are but I can’t do that with you talking & distracting me, understand?” His voice turned stern but I nodded obediently with a whimper. He kissed the fabric of my tie, separating my lips from his, making me flush & whimper longingly. “After all, it’s awfully rude for a student to disturb her professor, correct?” He smirked as his hand reached down and his thumb gently rubbed & teased my clit, eliciting another muffled whimper from my throat, and I nodded in agreement once more. He pulled my legs back where they dangled off the edge of his desk. He knelt down and supported my legs on his shoulders as his face leaned closer to my sex, and dragged his tongue slowly up my slit and gave my clit a flick with the tip. I couldn’t resist the moans coming from my lips as his tongue swirled and dipped into my folds, making me buck and writhe underneath him. He pursed his lips around my clit and began to suckle softly, and I had to bite back a squeal. Thomas chuckled, he could tell I was holding back. He began to suck harder and his teeth nipped at my flesh, making my back arch as I moaned and squealed loudly against the tie. He shifted slightly and I gasped as two of his long dexterous fingers plunged into me and started pumping in and out of my dripping cunt vigorously while he continued to lick & suckle my clit. My moans were becoming cries against my tie as he brought me closer and closer to climax, almost thrashing underneath this overwhelmingly pleasurable onslaught. Then he ceased everything, all movement and sensation stopped. He withdrew his face and fingers from my dripping slit, smiling down at me as he sucked my juices from his fingers & he grabbed a tissue from his desk and wiped my excess arousal from his beard. I whined with plea but Professor Hiddleston just smiled down at my writhing body, begging for release, enjoying my wanton state. He leaned down, letting his hands rest on my sides, and peppered little kisses from my chin and up my jawline, nipping at my earlobe. “This will be a lesson in delayed gratification, my love. I will not let you cum unless I’m ready to, understand?” His silken voice purred and I nodded with a whimper. “Good girl. Now, for session #2.” He spoke while pulling me off the desk completely, untying my wrists, and turned me so my back was to him. He took my hands again and retied my wrists behind my back, and then he splayed his hand across the small of my back as he pushed me down so my stomach was flat on his desk, positioning my legs apart. I couldn’t help but tremble with excitement and anticipation. “Relax, darling.” He whispered soothingly. I moaned delightfully as his hands gripped my ass cheeks, squeezing and massaging them, and it was purely blissful. I felt him push my cheeks apart and I shuddered, somewhat nervous as to what may happen next. The next thing I knew, I felt his beard and chin hair tickle my buttocks as I suddenly felt his hot tongue swirling and probing my backdoor. I squealed, trying to keep still as the strange foreign sensation overwhelmed me. He chuckled as he continued licking my anal ring, and inserted two of his long fingers in my pussy again, making me moan & relax. He slowly pumped his fingers in and out of me as his tongue teased and swirled around my backdoor. I quivered as the strange but wonderful stimulation started washing over me, making me moan and pant, my orgasm slowly rising again. I felt the muscles in my legs starting to tighten as my walls began to spasm around his fingers as I drew closer and closer and then… Nothing. His tongue and fingers stopped all motions and I whined loudly against my tie. “Patience, little one.” Professor Hiddleston chuckled and I heard the sound of a belt unbuckling and fabric shuffling. I moaned as I felt the velvety smooth shaft of his veiny cock grinding and rubbing between my ass cheeks, and shuddered as I could feel his hot breath panting against the flesh of my back. The tie around my mouth was removed and placed next to my head and Thomas leaned over me, growling behind my ear.

“Now, next question, darling…” He panted huskily.

“Y-yes, sir?” I panted, trembling.

“How do you want me to fuck you first?” He grasped his cock and rubbed against my cunt, making me whimper.

“Do you want me to take you here?” He pushed his head just past my labia and I moaned, longing for more.

“Or do you want me to take you here?” I squeaked when his head then pressed against the tight ring of my ass and whimpered.

“Please…” I panted, rocking my ass back against him needfully.

“Please, what… ?” He grabbed a fistful of my hair with a growl and I yelped.

“Fuck my cunt!” I cried out, and with that answer, he slammed his hips into me. I tried to scream out but his hand came around and clamped shut around my mouth, quickly muffling my pleasure-fueled cry.

“You must restrain yourself, darling.” Professor Hiddleston growled, thrusting into my pussy with a punishing tempo. My whimpers and moans were barely audible against his hand while he used his other to grasp my wrists as he braced himself while he rutted into me mercilessly. “Ah fuck, darling… Your cunt… Is just so… exquisitely tight.” He groaned through clenched teeth. With each thrust of his cock, my juices coated him for easier movement, hilting me each time and his sac would slap against me. His movements started to become shallow and harsher, hitting my cervix repeatedly, and only making me want to scream even more. Noticing I couldn’t restrain my noises, Thomas slid two of his fingers into my mouth and I eagerly sucked and licked them, moaning gratefully as he pumped into me. I felt my muscles tightening, wanting to orgasm desperately, but Professor Hiddleston made good on his word. He released my wrists to deliver a harsh smack across my right ass cheek and I squealed in surprise and slight pain. “Not yet, love. Not until I’m ready.” He growled, withdrawing his cock from my cunt and I couldn’t help but whine, feeling empty and yearning for more, desperate for release. However, my whining ceased and was replaced by nervous whimpers when I felt the head of his cock at my ass, prodding gently.

“Prof-Professor Hiddleston, I-I can’t… I don't know... If I can t-take you th-there…” I stuttered, shivering from nervousness as he gently pushed at my backdoor.

“Shhh, love. I’ll be gentle with this part of you.” He cooed, leaning over me and placed his hand over my mouth again to help muffle my ecstasy-fueled noises. He pushed in very slowly and I scrunched my eyes shut in pain at how stretched I felt. The further he pushed in, I whimpered louder, quivering from the fullness of the sensation, feeling stuffed beyond comprehension. I felt a small bit of comfort as Thomas kissed the back of my head tenderly, shushing me softly. “Nearly there, love.” He groaned, panting against my back. His crotch finally came to rest against me, his entire cock stuffed in my tight ass. “Such a good student.” He purred, nuzzling his face into my hair. For a brief moment, Professor Hiddleston remained completely still, letting me adjust to such girth, withdrawing his hand from my mouth to knead and massage my ass cheeks, relaxing me a little. I whimpered as he began to slowly pull out and push back in again in a slow rhythm. I started to moan at the strange but pleasurable sensation of being so filled, stretching and be stuffed over and over with his cock. “Oh God, Thomas…” I whispered huskily, pushing back against him a little and that bit of encouragement made him increase his tempo, slapping against my ass with more gusto. I started to lose control of my voice as he fucked me harder and faster. I bit my bottom lip hard, desperately fighting back my cries as I got closer. Once again, the bastard pulled out of me as I teetered on the edge, and before I could make any protest of frustration or anger, Professor Hiddleston flipped me over onto my back so I was now staring into his smoldering blue gaze, both of us panting and our skin was glistening with a sheen of sweat.

“Please… Professor Hiddleston…” I moaned, spreading my legs to give him an eyeful of my body. He inhaled a quivering breath with open lips, gazing upon my body & skimming his tongue over his lips to moisten them, drinking my image in. “Thomas…” My voice crooned softly, letting my feminine voice be heard in my most lustful plea. His eyes snapped upward to mine, his blue orbs bore into my soul with the same amount of aching lust and I knew what he wanted me to say. “Take me, please, Thomas.” I purred for him and he smiled sweetly. He reached over me and rummaged through his desk, withdrawing a foil packet. He ripped it open with his teeth and rolled a condom down his length. He pulled me close, settling between my spread legs.

“And take you, I shall, you beautiful woman.” With that, he thrusted into my hot wet entrance, making me moan loudly as he hunched over me, claiming my lips in a passionate kiss to hush my lust. As he undulated his hips, he swallowed my moans and his tongue toyed and danced with mine, his lips and tongue were gentler than our first kiss; the one action that started all this. I broke the kiss, gasping breathlessly as Thomas buried his face in the crook of my neck and shoulder. “Thomas, please…” I whimpered, writhing against the tie still restraining my wrists. “I want… I want to touch you.” I whispered and he hummed, kissing my cheek sweetly in response and he tickled me and made me giggle with that scruffy beard of his. He withdrew himself from me briefly, embraced me, and pulled me up swiftly, undoing the tie around my wrists, and I didn’t hesitate to slide off his coat and rip open his shirt, chuckling how the buttons went flying and clattered across the floor, revealing his lean and slightly muscular chest. I marveled at his handsome physique, running my hand up his chest and across his shoulder. He smiled, discarding his shirt, and laid me back down on his desk gently, letting me wrap my arms around him, feeling his muscles ripple and move underneath the flesh of his back. Once he re-entered my hot pussy, I moaned into his ear, letting my right hand tangle in his ginger hair.

“Oh Thomas…” I crooned, nuzzling into his hair while he began thrusting into me. “You are…” I breathed, trying to find my voice and words. “You make me feel… Like a real woman.” I moaned as he pumped himself in and out with more vigor, my climax was slowly rising.

“You are… truly lovely, my darling.” He groaned, peppering my jawline with kisses and little bites. “Th-Thomas…” I moaned, digging my nails into his skin, climbing higher & higher as my muscles began to tighten. He could tell what I wanted and groaned, driving into me hard and fast with everything he had.  
“Yes, love, cum, cum with me.” He panted and his words were my undoing. I bit down into his shoulder as I screamed, my pussy clamped around his cock as he pounded into me and made me cum hard as every muscle in my being tighten and my toes curled. As I spasmed, writhed, and moaned while I rode out my intense climax, Thomas growled as I came undone, his hips jerked and his tempo became erratic as he approached his own release. I felt him get closer as his cock twitched inside me and at the last second, he pulled out out of my cunt, tore the condom off, and released a copious amount of his hot cum onto my chest and stomach, groaning loudly through clenched teeth and his eyes scrunched shut tight as he squeezed and stroked every last drop of himself onto my skin. He dropped his exhausted body into his desk chair, handing me the tissue box to tidy myself up. As I wiped off him off my skin, I couldn’t help but giggle at a passing thought. Professor Hiddleston took notice and quirked an eyebrow at me with a curious lazy smile, watching me as I stood up and slipped my shirt back on.

"Something amusing, love?” He queried and I couldn’t resist a playful smirk spreading across my features, sliding my thong and pants up my legs and hips. I strode over to him, straddling myself on top of his lap as I draped my arms around his neck.

“If this is how you treat me when I dress like a man, I wonder how distracted you’ll be next week when I walk into your class wearing my favorite green plaid mini skirt, my tight black tank top with shiny thigh high black boots.”

“Oh sweet merciful God…” Professor Hiddleston groaned, wrapping his long arms around my frame and buried his face in my chest.

I’m going to wager the next day in his class will be most entertaining.


End file.
